Electrooxidative Fluorofunctionalization of Arylcyclopropanes

作者：Yanni Yue, Yang Song, Shuaishuai Zhao, Chi Zhang, Chuan Zhu, Chao Feng · 发表于：Organic Letters · 年份：2023 · DOI：10.1021/acs.orglett.3c02843 · 被引用次数：14 · 研究领域：Cyclopropane Reaction Mechanisms、Catalytic C–H Functionalization Methods、Sulfur-Based Synthesis Techniques

The work herein demonstrates the viability of an electrochemical oxidative protocol for the expedient realization of 1,3-fluorofunctionalization of arylcyclopropanes under catalyst- and oxidant-free conditions. Given the relatively low nucleophilicity of fluoride ion, the counterintuitive outcome that the ring-opening is initiated by nucleophilic fluorination is rationalized by invoking tight ion pair between aryl radical cation and BF 4 – counterion. By integrating alcohols, acids, and N-heterocycles as the terminating nucleophiles, straightforward 1,3-fluorooxygenation and 1,3-fluoroamination are smoothly achieved.